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Zinc‐Chloride‐Promoted Domino Reaction of Phenols with Terminal Alkynes under Solvent‐Free Conditions: An Efficient Synthesis of Chromenes
Author(s) -
Sreenivasulu Chinnabattigalla,
Satyanarayana Gedu
Publication year - 2018
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201800391
Subject(s) - chemistry , phenols , domino , lewis acids and bases , cascade reaction , substrate (aquarium) , organic chemistry , annulation , alkyl , zinc , chemical synthesis , solvent , acyl chloride , catalysis , chloride , combinatorial chemistry , oceanography , geology , biochemistry , in vitro
A domino one‐pot synthesis of 2 H ‐chromenes and 4 H ‐chromenes starting from phenols and terminal acetylenes in an atom economical reaction under solvent‐free conditions is described. This annulation reaction between phenols with alkynes is promoted by the simple Lewis acid ZnCl 2 . Significantly, to the best of our knowledge, the synthesis of 2 H ‐chromenes is the first of its kind, as it is based on the use of terminal alkyl acetylenes. The described method shows a broad substrate scope and good functional group tolerance.